Although there are a number of development approaches proposed in the decision support systems (DSS) literature, there appears to be a preference for prototyping over structured approaches. This paper describes the analysis stage of a DSS for the Property Development Department (PDS) at the Palmerston North City Council, New Zealand. The PDS role involves many ill-structured decisions with a large number of stakeholders. The paper describes the selection process for the methodology, analysing criteria for selection, and proposes a structured process for this analysis. The paper provides insights into when structured approaches are more appropriate for the development of DSS based on the type and complexity of the decisions supported